Bis(pinacolato) diboron (≥98%), Pd(dppf) Cl2•CH2Cl2, and 4-bromobenzonitrile (≥97%) were purchased from Matrix Scientific (Columbia, SC, USA). 1,4-Dioxane (≥99.0%) was purchase from J.T Baker (Phillipsburg, NJ, USA). 2-(4-Bromophenyl)ethanol (98%), K2CO3 (99.0%), triphenylphosphine (99.0%) and thiourea (99.0%) were purchased from Alfa Aesar (Haverhill, MA, USA). MgSO4 (97%), ethyl acetate (99%), Pd (PPh3)4 (99%) and tetrabromomethane (98%) were purchased from Acros Organics (Morris, NJ, USA). Hexanes (99%) was purchase from Macron Fine Chemicals (Phillipsburg, NJ, USA). Toluene (99.8%) and tetrachloroauric (III) acid (99.9%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Dichloromethane (99+%) was purchased from DUKSAN (Ansan-si, Korea). Sodium hydroxide (NaOH, ≥98.0%) was purchased from Fluka (St. Gallen, Swiss).
Triphenylphosphine
Manufactured by Thermo Fisher Scientific
Sourced in United States, Belgium
Triphenylphosphine is a chemical compound commonly used as a reagent in organic synthesis. It is a white crystalline solid with the molecular formula PPh3. Triphenylphosphine serves as a ligand in organometallic chemistry and is a useful reducing agent in various chemical reactions.
Automatically generated - may contain errors
Lab products found in correlation
Ethyl acetate, by Thermo Fisher Scientific (3 mentions)
2 iodobenzonitrile, by ABCR (2 mentions)
Thiourea, by Thermo Fisher Scientific (1 mentions)
Dichloromethane, by Duksan Pure Chemicals (1 mentions)
Tetrachloroauric 3 acid, by Merck Group (1 mentions)
Mgso4, by Thermo Fisher Scientific (1 mentions)
K2co3, by Thermo Fisher Scientific (1 mentions)
Toluene, by Merck Group (1 mentions)
Sodium hydride, by Merck Group (1 mentions)
Lithium hydroxide monohydrate, by Thermo Fisher Scientific (1 mentions)
Celite, by Merck Group (1 mentions)
Hydrazine monohydrate, by Merck Group (1 mentions)
Methyl iodide, by Merck Group (1 mentions)
Silver 1 carbonate, by Merck Group (1 mentions)
Toluene, by Sinopharm (1 mentions)
Methanol, by Sinopharm (1 mentions)
Sodium borohydride, by Sinopharm (1 mentions)
N hexane, by Sinopharm (1 mentions)
Trifluoroacetic acid, by Iris Biotech (1 mentions)
Sodium bicarbonate, by Thermo Fisher Scientific (1 mentions)
13 protocols using triphenylphosphine
1
Synthesis of 4-Bromobenzonitrile Derivatives
2
Synthesis of Indolo[2,3-d]benzazepinone Derivatives
3
Synthesis of Fluorinated Monomers and Precursors
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Potassium permanganate, 2-5-Dichlorotoluene pyridine, thionyl chloride, carbon disulfide, benzene, aluminum chloride, chlorosulfuric acid, hydrochloric, nickel bromide, zinc powder, and triphenylphosphine were received from TCI, Sigma-Aldrich, and Alfa Aesar. Dimethylsulfoxide (DMSO), dimethylacetamide, dichloromethane, methanol, ethanol was used as received. The 2,5-Dichlorobenzophenone (DCBP) monomer, precursor’s fluorosulfonyl isocyanate (FSO2NCO), and sulfamoyl fluoride (FSO2NH2) were synthesized with high purity and yield (Schemes S1–S3 and Figures S1–S3 , respectively).
4
Synthesis of Functionalized Chalcogenides
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All the following reagents were purchased and used as received without further purification. Cuprous bromide (CuBr, 99%), sodium borohydride (NaBH4, 98%), methanol (CH3OH, analytical grade), toluene (C7H8, analytical grade) and n-hexane (C6H14, chromatographic grade) were purchased from Sinopharm Chemical Reagent Co. Ltd. Acetonitrile (CH3CN, analytical grade) and dichloromethane (CH2Cl2, analytical grade) were purchased from Kermel. 2-Chloro-4-fluorobenzenethiol (C6H4ClFS, 97%) and triphenylphosphine (PPh3, 99%) were purchased from Alfa Aesar. All glassware was cleaned with aqua regia (v(HCl)/v(HNO3) = 3 : 1), rinsed with ultrapure water, and then dried in an oven prior to use.
5
Synthesis of Diverse Pyridyl-Substituted Indole Scaffolds
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5-Nitro-1H-indole-3-carboxaldehyde,
2-iodobenzonitrile, and silver(I) carbonate were purchased from abcr.
1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI·HCl)
and trifluoroacetic acid were purchased from IRIS biotech, while palladium
(10%) on activated charcoal, tert-butyl dicarbonate
(Boc2O), palladium(II) acetate, 4-(dimethylamino)pyridine
(DMAP), sodium chlorite, and sulfamic acid were obtained from Sigma-Aldrich.
2-Formylpyridine, absolute dimethylformamide (DMF), tetra-n-butylammonium fluoride (TBAF), 4-toluenesulfonyl chloride, triethylamine,
sodium bicarbonate, magnesium sulfate, and borane solution (1 M in
THF) were bought from Fisher/Acros Organics. Triphenylphosphine, sodium
bicarbonate, and celite were purchased from Alfa Aesar. 2-Iodobenzeneethylamine
was prepared by using a literature protolol.28 (link)Synthesis of the main organic scaffoldsb 1 –h 3 is described in detail in the Supporting Information . 1H NMR spectra of intermediate species b 1 , b 2 , c 1 –c 3 , d 1 –d 3 , e 1 –e 3 , f 1 –f 3 , g 1 –g 3 , h 1 , and h 2 are shown in Figures S36–S54 .
2-iodobenzonitrile, and silver(I) carbonate were purchased from abcr.
1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI·HCl)
and trifluoroacetic acid were purchased from IRIS biotech, while palladium
(10%) on activated charcoal, tert-butyl dicarbonate
(Boc2O), palladium(II) acetate, 4-(dimethylamino)pyridine
(DMAP), sodium chlorite, and sulfamic acid were obtained from Sigma-Aldrich.
2-Formylpyridine, absolute dimethylformamide (DMF), tetra-n-butylammonium fluoride (TBAF), 4-toluenesulfonyl chloride, triethylamine,
sodium bicarbonate, magnesium sulfate, and borane solution (1 M in
THF) were bought from Fisher/Acros Organics. Triphenylphosphine, sodium
bicarbonate, and celite were purchased from Alfa Aesar. 2-Iodobenzeneethylamine
was prepared by using a literature protolol.28 (link)Synthesis of the main organic scaffolds
6
Liposomal Nano-formulation Development
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Lipoid S100 (Soya Phosphatidvl Chdiae) was purchased from Lipoid (Ludwigshafen, Germany). Cholesterol (CHOL) and 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) were purchased from Avanti Polar Lipids (Alabaster, USA). 1.2-Dipalmitoyl-sn-glycero-3-phospho-ethanolamine (DPPE) was purchased from Corden Pharma Switzerland LLC (Switzerland). DSPE-mPEG2000 was purchased from Shanghai YuanYe Bio-Technology Co., Ltd (Shanghai, China). Triphenylphosphine and 3-bromopropylamine hydrobromide were obtained from Alfa Aesar (USA). RA-XII was isolated from R. yunnanensis and identified by mass spectrometry (MS) and nuclear magnetic resonance (NMR) by us. Sodium hyaluronate (molecular weight: 5.6 kDa) was purchased from Shandong Freda Biopharmaceutical Co., Ltd. (Shandong, China). 3,3ʹ-Dioctadecyloxacarbocyanineperchlorate (DiO) was obtained from Sigma-Aldrich (St Louis, MO, USA). MitoTracker Red, MitoTracker Green, Hoechst 33342, LysoTracker Red and Annexin V-FITC/PI cell apoptosis kit were purchased from Invitrogen (Carlsbad, CA, USA). Calcein-AM/PI Cell Viability/Cytotoxicity Assay Kit and ROS Assay Kit were purchased from Shanghai Biyuntian Biotechnology Co., LTD (Shanghai, China). Ultrapure water was prepared using a Millipore Simplicity System (Millipore, Bedford, USA).
7
Metabolite Identification via LC-MS
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LC–MS-grade water and acetonitrile (ACN) were purchased from Fisher Scientific (Houston, TX); triphenylphosphine (TPP) and 2- hydrazinoquinoline (HQ) from Alfa Aesar (Ward Hill, MA); 2,2′-dipyridyl disulfide (DPDS) from MP Biomedicals (Santa Ana, CA); tylosin tartrate from Ark Pharm (Arlington Heights, IL); acetic acid-d4 from Sigma-Aldrich (St. Louis, MO); glycocholic acid-13C1 from C/D/N Isotopes (Quebec, Canada). The metabolite standards used for structural confirmation were from Sigma-Aldrich, Fisher Scientific, AlfaAesar, Ark Pharm (Libertyville, IL), respectively.
8
Synthesis and Characterization of Gold Nanoparticles
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Hydrogen tetrachloroaurate (99.9%, Strem
Chemicals), triphenylphosphine (99%, Alfa Aesar), sodium borohydride
(98%, Aldrich),l -glutathione reduced (>98%, Aldrich),
40%
19:1 acrylamide:bis(acrylamide) solution (Biorad), ammonium persulfate
(≥98%, Sigma), TEMED (≥98%, tetramethylethylenediamine,
Biorad), Tris Base (≥99%, CalBioChem), hydrochloric acid (≥99%,
EMD Millipore), and glycine (≥98.5%, J.T. Baker) were used
as received. Sephadex G-50 Superfine was purchased from GE Healthcare.
Silica gel (grade 62, 60–200 Mesh) was purchased from EMD.
Thiocholine (N,N,N-trimethylammoniumethanethiol, TMAT) trifluoroacetate was synthesized
according to the published procedure.51 (link),52 (link) Dichloromethane
was distilled from calcium hydride prior to use. CHCl3 was
run through a plug of basic alumina prior to use. 18.2 M Ω-cm
deionized water was used for all synthetic and purification processes.
Au(PPh3)Cl was synthesized from HAuCl4 and PPh3 according to a known procedure.53 All other reagents and solvents were purchased from Aldrich or Mallinckrodt
and used as received.
Chemicals), triphenylphosphine (99%, Alfa Aesar), sodium borohydride
(98%, Aldrich),
40%
19:1 acrylamide:bis(acrylamide) solution (Biorad), ammonium persulfate
(≥98%, Sigma), TEMED (≥98%, tetramethylethylenediamine,
Biorad), Tris Base (≥99%, CalBioChem), hydrochloric acid (≥99%,
EMD Millipore), and glycine (≥98.5%, J.T. Baker) were used
as received. Sephadex G-50 Superfine was purchased from GE Healthcare.
Silica gel (grade 62, 60–200 Mesh) was purchased from EMD.
Thiocholine (N,N,N-trimethylammoniumethanethiol, TMAT) trifluoroacetate was synthesized
according to the published procedure.51 (link),52 (link) Dichloromethane
was distilled from calcium hydride prior to use. CHCl3 was
run through a plug of basic alumina prior to use. 18.2 M Ω-cm
deionized water was used for all synthetic and purification processes.
Au(PPh3)Cl was synthesized from HAuCl4 and PPh3 according to a known procedure.53 All other reagents and solvents were purchased from Aldrich or Mallinckrodt
and used as received.
9
Synthesis and Cell Viability Assay of dPG Compounds
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All chemicals were purchased from Merck KGaA, Darmstadt, Germany and/or its affiliates and used without any further purification, unless otherwise stated. The solvents used herein, i.e., diethyl ether (100%) and N,Ndimethylformamide (99.8%) were bought from VWR chemicals and Acros Organics, respectively, while DCM (99%) and ethyl acetate were both obtained from Fischer Scientific. Sodium hydroxide in the form of pellets, as well as in a 99.5% solution, was also procured from Fischer Scientific. Triphenylphosphine (99%) was purchased from Alfa Aesar. dPG of ≈6 kDa average molecular weight was prepared as previously reported [22] [23] [24] with the improved method. [25] For purification carried out with dialysis, Spectra Por dialysis tubing (MWCO = 2000 g mol -1 ) (Carl Roth GmbH, Karlsruhe, Germany).
Cell viability assays were performed with a CCK-8 Kit from Sigma Aldrich according to the manufacturing instructions. A549, HBE, HeLa, and Vero E6 cells were obtained from Leibniz-Institut DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH and cultured in DMEM supplemented with 10% (v/v) FBS, 100 U mL -1 penicillin and 100 µg mL -1 streptomycin.
All chemicals were purchased from Merck KGaA, Darmstadt, Germany and/or its affiliates and used without any further purification, unless otherwise stated. The solvents used herein, i.e., diethyl ether (100%) and N,Ndimethylformamide (99.8%) were bought from VWR chemicals and Acros Organics, respectively, while DCM (99%) and ethyl acetate were both obtained from Fischer Scientific. Sodium hydroxide in the form of pellets, as well as in a 99.5% solution, was also procured from Fischer Scientific. Triphenylphosphine (99%) was purchased from Alfa Aesar. dPG of ≈6 kDa average molecular weight was prepared as previously reported [22] [23] [24] with the improved method. [25] For purification carried out with dialysis, Spectra Por dialysis tubing (MWCO = 2000 g mol -1 ) (Carl Roth GmbH, Karlsruhe, Germany).
Cell viability assays were performed with a CCK-8 Kit from Sigma Aldrich according to the manufacturing instructions. A549, HBE, HeLa, and Vero E6 cells were obtained from Leibniz-Institut DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH and cultured in DMEM supplemented with 10% (v/v) FBS, 100 U mL -1 penicillin and 100 µg mL -1 streptomycin.
10
Synthesis of Organic Compounds Using Common Reagents
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1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, > 97%), 4-dimethylaminopyridine (DMAP, ≥ 99%), ethanolamine (≥ 99%), sodium methoxide (NaOMe, solution 0.5 M in methanol), n-butyllithium (n-BuLi, solution 2.5 M in hexanes), thionyl chloride (SOCl2, ≥ 99%), anhydrous lanthanum triflate (LaTf3, 99.999%), anhydrous lanthanum chloride (LaCl3, 99.9%), methyl tosylate (MeOTs, 98%), anhydrous benzotrifluoride (≥ 99%) and dodecylamine (98%) were purchased from Sigma Aldrich. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU, 99%) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 98%) were supplied by Alfa Aesar. N,N′-Dicyclohexylcarbodiimide (DCC, ≥ 99%) was purchased from Fluka and triphenylphosphine (PPh3, 99%) was supplied by Acros Organics. The other solvents were supplied by Scharlab. Furthermore, toluene, dichloromethane (DCM), dimethylformamide (DMF) and ethanolamine were dried before use according to literature35 .
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